Hydrochloric Acid → HCID 131719923, compound

HRID 363413Notes

Reaction equation

HRID 363413 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@@H:15]([C:17]([NH:19][CH2:20][C:21]([O:23]CC1C=CC=CC=1)=[O:22])=[O:18])[CH3:16])=[O:13])=[O:9])[CH3:7])=[O:4].[ClH:31]>C(O)(=O)C>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@@H:15]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[CH3:16])=[O:13])=[O:9])[CH3:7])=[O:4].[ClH:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131719925HCID 131719925, compound

Product 1

HCID 131719923HCID 131719923, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To Gly-Ala-Gly-DAla-Gly-OBzl prepared as in Example 34C (13.4 g, 25.7 mol) in glacial acetic acid (400 ml) was added concentrated HCl (100 ml) and the reaction mixture was stirred at room temperature for 24 h. The solution was concentrated in vacuo, dissolved in water (100 ml) and the resulting aqueous solution was washed with ether (2×50 ml) and concentrated again in vacuo. Drying at high vacuum afforded 9.70 g (100% yield) of the product as a white powder: 1H NMR (D2O) δ 1.38 (d, J=7.2 Hz, 3 H), 1.39 (d, J=7.2 Hz, 3 H), 3.84 (s, 2 H), 3.92 (s, 2 H), 3.96 (s, 2 H), 4.34 (m, 2 H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutiondissolved in water (100 ml)
  3. washthe resulting aqueous solution was washed with ether (2×50 ml)
  4. concentrationconcentrated again in vacuo
  5. customDrying at high vacuum

Sources & evidence

ORD record
ord-296b5cf1cc16453e9c7a95e7ba8041bb
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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